What Men Find Behind Female Masks

Inside the increasingly common practice—and business—of female masking
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Kerry, the "unofficial matriarch" of the female-masking scene

Julie, an immaculately made-up woman, sits down in front of a camera. She has thick, voluminous hair that frames the high cheekbones of her conspicuously crease-free face. Her elegant, arched eyebrows and extra-long eyelashes act as a counterbalance to her plump, painted lips. She looks out of frame, as if admiring herself in a mirror, before giggling and batting her eyelids.

“Oh dear,” she purrs, tilting her head from side to side. “Another long day in a wig and a girdle.”

She reaches up and emits a light moan as she unclips her gold earrings and gently sets them aside, one by one. She considers her image a few moments longer, then places her hands just below her ears and begins to pull her blemish-free skin off and away from her jawline. It’s only now that we realize it’s not human skin, but rather a mask made of soft, flesh-like silicone rubber.

Julie is one of the most visible faces of female masking, a specific subset of cross-dressing men who wear masks, and occasionally skin-tone bodysuits, to make them look more like biological women. The videos that she uploads to YouTube have received hundreds of thousands of views, attracting both fans and detractors.

Julie is but one of scores of maskers around the globe; the most popular masking website, Dolls Pride, has almost 10,000 active members. But, until now, the subculture has remained relatively unknown outside the tight-knit community. Even the nation’s foremost experts on sexuality haven’t heard of masking (though it’s worth noting that the practice isn’t always sexually motivated).

“I just checked with Dr. Kaplan and neither one of us have heard this term before,” said Dr. Richard Krueger, who, with Dr. Meg Kaplan, heads up the Sexual Behavior Clinic at the New York State Psychiatric Institute.

This doesn’t surprise Kerry. At 52, he has been masking for 37 years and is considered by many to be the unofficial matriarch of the scene. He says that while there are magazines featuring maskers that date as far back as the 1930s, the practice has existed largely on the fringe of society.

“I've got a fetish book from the 1940s and '50s of people doing female masking back then, so by no means did we invent anything,” he said. “Our grandparents were doing this.”

He explains that masking first entered his consciousness when he saw an episode of Mission: Impossible in 1970—there were 10 episodes between 1969 and 1973 that saw actresses Lynda Day George, Lesley Ann Warren, and Barbara Bain wearing masks to impersonate other characters. Intrigued by the idea of transformation, Kerry would sit and look at his third-grade teacher in amazement, wondering what it would be like if her face were a mask.

“She was blonde and she had low-cut dresses for the 1970s, and I'd sort of think if she was wearing a mask it would have to extend all the way down her neck,” he said. “And I remember having that thought, if her head was a mask she'd have to have it going all the way down into her dress.”

Seven years later at 15, he began experimenting himself. He scoured local costume shops and found two relatively simple masks that he customized to fit his needs. He says he was insecure growing up and that wearing a mask offered him the chance to recreate himself and become someone who didn’t care what others thought.

“It'd be one thing to disguise myself as a guy, but I'd still be a guy,” he said. “But if I could disguise myself as a woman that would be a total transformation.”

It soon became sexual and he would retreat to his room, put on a mask and masturbate. He says it wasn’t the idea of womanhood that aroused him; it was the masks themselves. “I mostly did think about masks when I was masturbating,” he said. “I never masturbated over naked girls in Playboy or anything like that.”

Still, for Kerry, the guilt that can surround teenage sexuality was compounded by the sense that his preference was extremely unusual. “I thought that I've got to be the only person on the planet that has these feelings and these interests,” he said. It wasn’t until the birth of the Internet two decades later that he discovered there was a thriving community of men who also enjoyed wearing female masks—which offered him both solace and an exciting business opportunity.

There hadn’t been many developments in the masking world in the intervening 20 years. The two masks Kerry wore during this period were a heavily customized Bride of Frankenstein creation and a blonde woman forever smoking a cigarette. So, disappointed by the dearth of available options, he set about making his own.

It wasn’t long before he started selling them to other maskers. His side business became so successful that he quit his day job as a printer and turned a room of his Seattle home into a masking workshop, much to the chagrin of his wife of 12 years.

“She thinks it's weird,” he explained, adding that she steers clear of the workroom and its row upon row of female faces. “She doesn't have anything to do with it. Once in a while she might help me with something but it's not really her thing.”

Her response also quashed the possibility they’d incorporate masking into their sex life, which Kerry insists is a good thing. “It's one of those things where we all sort of have fantasies, scenarios we'd like to do but I think the reality would be really, really disappointing. So probably better not to try that,” he said.

“In a way I don't want to fetishize my wife. You know, I have sex with my wife because I love her. And I don't want to turn her into a sex object, if that makes any sense at all. Because the mask is a fetish object, that's the only thing it really exists for.”

He believes his wife’s discomfort reflects society’s attitude toward masking, even if people know about it it’s not something they openly discuss. “A lot of people are very creeped out by the whole masking thing,” he added. “It'd be the same as talking about autoerotic asphyxiation, no one wants to talk about it, you don't want to read about it, and you don't want to hear about it, it's just not part of polite company.”

But that hasn’t stopped those at the vanguard of popular culture from taking note of Kerry and his masked brethren. Fashion photographer Steven Meisel shot women in female masks for Vogue Italia in 2012 after coming across videos online. Actress Jamie Brewer also wore a female mask during the Halloween episode of Ryan Murphy’s American Horror Story, screen grabs of which were taken and quickly shared among members of the masking community.

These non-judgmental representations are considered a welcome departure from what’s usually on offer. Masks are a familiar trope used in horror movies to build fear around the concept of the unknown, and Silence of the Lambs took things one step further, with serial killer Buffalo Bill skinning his female victims to make a bodysuit—not entirely dissimilar to the silicone ones maskers sometimes wear. Kerry believes the association helps to demonize and further marginalize maskers, though he’s not completely humorless about it. “If I had him as a customer we would have saved all those girls lives,” he laughed.

While most maskers realize the practice is not broadly accepted, the criticism they get from others within the fetish community, as well as non-masking cross-dressers, carries a particular sting.

“It does strike me odd though that people who practice some of the most socially unacceptable behaviors can also be the most prejudiced,” said T-Vyrus, 34 “in doll years,” a self-described “drag queen, tranny, female masker” and editor of masking magazine Hot Girls. “Among cross-dressers, shemales, trannies and the like, there is often the thought that masking isn't real, that it's a put on, a surrogate, a farce. The thought that if a person were truly serious, they wouldn't hide behind a mask.”

Lisa

This fear of rejection is what keeps truck driver Lisa, 47, from wearing a mask in public. Like Kerry, she identifies as a heterosexual man and maintains an active “male life” during the day, but uses the female pronoun when she transforms into Lisa, his alter ego, at night. She lives with her two sisters in New Jersey, and though they are aware of what their brother gets up to behind a locked bedroom door, it’s never discussed.

She never openly masks around the house and wouldn’t think to step outside. Apart from the fact that her six-foot-two, 260-pound frame would be a dead giveaway, Lisa’s reluctance to come out is bolstered by the belief that her brother’s attempts to pass as a woman in public are what led to his drug overdose.

Lisa said she realized her brother, Mike, was interested in women’s clothing when she came home one day to find him dressed in a French maid costume. Their father had originally bought the outfit to wear on Halloween, the only time that he could openly indulge his own interest in cross-dressing—it was an open secret that all three men in the family liked to wear women’s clothes.

“It's in our blood,” said Lisa, adding that they never spoke of it. “I come from a very hard-working, blue-collar, macho family, and it was never discussed, ever.” Her sister would often come to her to complain about missing clothing, demanding to know what had happened to it. “I told her, 'I didn't do it,’” she said. “And I didn't, it was my brother!”

Mike was the most audacious, according to Lisa. He would venture outdoors dressed in full drag, despite the fact that he was “taller and bigger” than everyone. “He's a very big man,” she said. “So for him to actually try to pull off looking like a woman … I hate to say it but that wasn't going to happen.”

His bravado ended up costing him. Mike decided to come out to some friends, and it resulted, Lisa believes, in his death. “He told a few people and when they got mad at him they told everybody,” she said. “And right away, he's a pervert, he's a loser, he's gay, and all that, you know? And I don't think he dealt with that too well. He ended up taking drugs and ended up dying because of that.”

For her part, Lisa is content to stay indoors and speak to her masking friends online. She admits it can be lonely, but adds that her masks offer some consolation. “I have trouble with girlfriends and I think it helps fill the void of not having a female around,” she said. “I create that kind of entity in myself when I don't have that companionship.”

She has, however, struck up a close friendship with one particular masker, and they chat three or four times a week. Though she says she’s not into it, Lisa agrees to act out the role-playing scenarios that have come to define their friendship.

“There's one guy who calls me Mommy,” she said. “He thinks I'm his mother. He wants to be the daughter. I kind of actually feel squeamish about the whole thing, but I feel sorry for the guy  I feel bad because I don't think he has anybody to talk to, as I really don't either. So we keep each other company by talking to each other.”

Though Lisa has no plans to out herself in the immediate future for fear of losing what she has “on the other side of the mask,” she hopes that things will change to the point where she’ll be able to pluck up the courage to one day reveal herself. “There are senators out there doing this too, you know. Judges, police officers, every walk of life,” she said. “It's just something that we do to pretty much escape reality sometimes.”

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Luke Malone is a journalist and producer based in New York. He recently produced a forthcoming documentary on masking, Secrets of the Living Dolls.

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